Lollapalooza time again! In this corner, we've got jammin' music stages all over Grant Park to the north of Buckingham Fountain, in the opposite corner, we've got equally rockin' stages to the south. But what are you gonna do when you've got a mile between you and your new favorite band? Read on, and get ready to duke it out.

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Friday

2/2:15-2:30/3:15 - The Terrible Twos vs. The Go! Team

Though the kids could get into The Go! Team's dance-pop and rah-rah cheers, there's no way you can compete with a band whose latest album features a song called "Great Big Poop" (which, as some parents may know, earns its own kind of rah-rah cheer!). Headed by former New Amsterdams member Matt Pryor, The Terrible Twos are one of kiddy pop's rising stars — the band's new album, Jerzy The Giant (out this week on the pop-punk label Vagrant), is a charming collection of songs about letters (consonants, specifically), funny creatures and, of course, poop. It ain't so terrible being two, after all, and all kid's music doesn't have to be terrible, either — along with the Twos, this year's Lolla Kidz stage could also entertain those not toting tots. The Terrible Twos, "Math Stomp" [mp3]
-JP Pfafflin

2:30-3:30 - Jeff Tweedy / Rogue Wave vs. Holy Fuck

The rock band / kiddie act crossover is more and more common these days, with moms and dads in bands entertaining their own lil' guys with family-friendly music that won't have you teeming with road rage after hours in a car with Radio Disney on the dial. One such band making the leap from clubs to cribs is darling indie-rockers Rogue Wave, who recently contributed to the comp, For The Kids Three. Wilco frontman Jeff Tweedy is also no stranger to the kids' circuit — he's played shows to support The Old Town School of Folk Music's Wiggleworms, the school's program for wee ones, of which Tweedy's children are former students (they've since gone on to start their own rock band). And while Holy Fuck is probably the most family-unfriendly name at the festival, they're an electro-party rock force not to be missed, and play earlier in the day at the AT&T stage at 1:15pm. So, you can have your cake and eat it, too, Mom and Dad.
-JP Pfafflin

3:15/3:30-4 - Tiny Masters of Today vs. Louis XIV

Memorable Pitchfork reviews aside, it's probably true that the dudes in Louis XIV couldn't hold their own court against the (pre-) teens in the Brooklyn-based duo of Tiny Masters of Today. The siblings of Ivan and Ida — 14 and 12 years old, respectively — made their debut in 2005 with the basement single and anti-Bush ode, "Bushy" [mp3] (See also: Midwestern 'tween punks Old Skull who ranted against Reaganism in the '80s) and gained the attention of Jon Spencer Blues Explosion drummer Russell Simins, who toured with the band last year. The band released its debut album, Bang Bang Boom Cake, in 2007, and featured collaborations with Kimya Dawson, the B-52's Fred Schneider and Yeah Yeah Yeah's Karen O and Nick Zinner.
-JP Pfafflin

4:15-5:15 - Black Keys vs Gogol Bordello

The two-man Akron-based garage rock band and the 10-person self-described gypsy punk group from New York don't have a whole lot in common. One is a lo-fi blues-influenced rock duo with no gimmicks. The other is a cacophony that's only really worthwhile when seen. If you want to see and hear efficiency in music, you will see the Black Keys, who have the distinction of playing Lollapalooza back-to-back years now. These two men produce a sound so thick you'll swear there're more than just two of them. Unfortunately, as good as they are, they're not much to look at. Gogol Bordello, on the other hand, puts on a very entertaining show and you won't walk away feeling like you missed out on anything once they're done. (In a strange coincidence, both bands are headlining post-Lollapalooza shows. So if you miss one at the festival, try to see them at Metro.)
-James Ziegenfus

5:15-6:15 - Cat Power vs. Grizzly Bear

Grizzly Bear are riding strong after a slot on David Letterman last week and as we speak an opening gig for Radiohead on the rest of their tour this summer. Oh Grizzly Bear, how you've grown since that one album two years ago. The ironic thing, however, is that they haven't grown much (they've only added one EP to their catalog since that 2006 album Yellow House). Instead, people have just started noticing. The album itself is a bit lazy, the songs take their whole life to develop, but that's one of the better reasons to go watch them get created and killed right in front of you. Cat Power has not had the best reputation for live performances as of late. Her songs tend to lose their air as she flits around the stage. The blues band she's been touring with, luckily, is spot on for themselves, and it's great as a satisfier for your own personal interest to hear some of her older songs transformed with this new style. Neither of these bands are set out to wake you up, incase you were looking for that. Instead, take a late afternoon nap in the grass circling these performers, chill out to the tunes, and rest up for Radiohead later that night. And for this purpose, choose Cat Power, she's simply more talented.
-Emily Kaiser

5:15-6:15 - Mates of State vs. Million $ Mano

So here’s a hipster dilemma: do you go for the tried and true harmonies of the adorable pair that make up Mates of State, or do you settle in at the DJ stage to hear Chicago son and up-and-comer Million $ Mano? The Mates, hopefully enjoying a broader fan base after their national tour with Ira Glass and "This American Life" last year, are favorites with the head bobbing, foot shuffling set, while M$M is the darling of the bustling Chicago electro/hip-hop scene. This set will likely come down to how mellow or amped you want to be heading into Friday night. Do you want to pace it with the delightfully talented husband and wife team jamming away on their drums and keys? Or do you want to get a little funky over at Perry's tent with some Daft Punk-influenced beats and a hometown flava?
-Anne Holub

"Returning" to lollapalooza are last year's no shows, CSS from Sao Paulo. With Brazilian flair, punk attitude, and an electro-clash style, CSS will bring an energetic and wild sound to the lolla crowd. Their sophomore album, Donkey, was just released on July 22nd. Back in 2006, they played a small side tent at Pitchfork and the lead singer Lovefoxx got so wild and out of control, she jumped off the stage and broke her arm. Expect random, crazy, raw, and without question the best performance of the day.

Mickey Rocks and Chuck Inglish (aka The Cool Kids) are two of the hottest names in Chicago right now, and being from Chicago means they will be back through again. So why pass up another band to catch them? However there is nothing like feeling that wave of bass in your face, and some of my favorite acts of all time have been hip-hop acts. Also, I am interested in seeing what these two will be wearing. If there is one thing that this new era of hip-hop brings it is some of the craziest retro fashions around. Yet, just like with Kid Sister you make have to pass on these hometown boys.

Stephen Malkmus, two words, legendary and rejuvenated. Stephen has somehow survived the weird and awkward electro phase and has found new life with The Jicks and his latest release, Real Emotional Trash (Matador Records, March '08). If you are a hardcore pavement fan, as many are, I may not be able to sway you, but if you are looking for energy and excitement this set may disappoint.

Jack White can do no wrong. Is that an accurate statement? He certainly has put together an impressive catalog with The Raconteurs and The White Stripes. Over the years both he and Brendan Benson have become accomplished performers and always play with passion and energy. Their latest album Consolers of the Lonely was surprisingly released last March, and it has only worked to expand their fan base. This is the main reason why you may need to take a pass on Jack White and the boys. The crowd may limit how enjoyable the performance will be for you. For the smaller crowd and an energetic performance I would recommend checking out CSS.
-Jason Behrends

Saturday

12:30-1:30 - Does this Offend You vs. The Postelles vs. The Ting Tings

When I first heard The Ting Tings first single "Great DJ" I was really impressed. It was catchy, dancy, fun and it made me want to scream-along. Then I heard their second single, "That's Not My Name", and I bobbed my head with a half smile and a puzzled brow. Not that it was identical, but the formula was the same. We are not even going to talk about "Shut Up and Let Go". So does this band have staying power? Will you look back next summer and say, who was that band that I saw on Saturday morning? What ever happened to them? Yes, they are fun danceable pop, but outside of the three above tracks their album, We Started Nothing, is pure fluff.

Also playing Saturday morning are New York's The Postelles, no not The Fratellis that was last year, although the two bands are similar. They play that speed-up fifties crooner brand of pop music. Yes, much like The Strokes, and no they are not as good as The Strokes. However, Albert Hammond Jr. did produced one of their single. They are a fun and aggressive young band playing in an earlier spot with something to prove. All of those factors could result in a very entertaining set.

There is nothing not to love about UK electro freaks Does it Offend You, Yeah? Their sound may not be unique, but it is extremely fun to listen to. From the pure glitch and big beat of "We Are Rockstars" to the distorted vocals of "Doomed Now", their music will make you move. Besides any band with a song called "Attack of the 60 Ft Lesbian Octopus" has to be witnessed live. Taking their name from the British version of The Office and a line delivered by Ricky Gervais, Does it Offend you, Yeah? mixes organic instruments with their electronic beats to create a forceful sound and a more enjoyable live performance. This band is the reason you should get out of bed early on Saturday morning.
-Jason Behrends

1-2/1:30-2:30 - Devlin & Darko vs. Mason Jennings

Okay, so Mason has a few more people citing his critical acclaim — the Minnesota City Pages named him the "Artist Picked To Click", the Boston Phoenix named him "Best New Band" from Hawaii, and he's toured with this summer's unexpected festival must-have, Jack Johnson. But check it out: this is Chicago, what the hell does Boston know about Hawaii? and this thread should answer all of those points nicely.

Now lets look at the alternative, because oh baby, is there one: Devin and Darko, the boys behind the fat, Crisco-covered beats that had you all banging heads and otherwise over the past year or two. Now its not like you can't see the whole enchilada of Naheem and the Gang later on in the fest, but as of late, D&D have been making some absolutely s%#$-hot remixes that are tearing up dance floors so grimy they're not even level anymore. Lollapalooza is not exactly known for drawing the most elite music snob crowd, and the daylight and extreme heat will cramp the club-kids style. But if you push up front and get that ba-donk-a-donk of yours moving along with what they're spinning, you may find it all very worth it.
-Dan Morgridge

3:30-4:30 Devotchka vs. MGMT

Devotchka is that band that plays all the eastern European songs that wrenched your heart out during Little Miss Sunshine. MGMT is that band that you are waiting for your friends to pronounce out loud first just incase you've been saying it wrong in your head. MGMT has had a huge year already, with Oracular Spectacular storming into our 2008 surrounded by hype, most of it deserved. From afar their blinding live acts looks like the biggest party around, but get a bit closer and you sense an underlying hollow-ness, a fault of the music itself more than anything else. Devotchka plays the exact opposite, storming in solitude from a single spot on stage while they produce a slightly foreign (might be the accordian) but personally touching string of songs. They might not be as fun as MGMT, but that's the price you pay for trying to say something. Substance over showmanship hands this favor to Devotchka.
-Emily Kaiser

4:30-5:30 Brand New vs. Explosions in the Sky

The first image that comes to mind when I think of these two bands in a death match involves a case of PBR and a Halo showdown. While they are certainly not as "Bro"-ed out as the picture I just painted, they are probably asked to hold down that demographic more often then they'd like. For Explosions in the Sky, they can thank the Friday Night Lights soundtrack they are so wonderfully responsible for. For Brand New, it's their ability to write the lyrics you wished you could (or did) sing to your high school girlfriend. Either way both these acts rise above any image you'd like to have of them the second they start playing. Explosions dominates all sensory perception with their doomsday-instrumental jams. Unfortunately the bigger the space, the more Explosions are unable to fill it, and at such a huge festival in such a wide open outdoor space, you'll probably end up noticing just how small the band actually is and once again bedisappointed by reality. Brand New has skyrocketed this last year or so since 2006's The Devil and God are Raging Inside Me showed how much they matured and began to earn them some real credibility. Thought to be plagued by beach angst and a pledge to "stay 18 forever", Brand New is still angry, but expresses it with such a desperate fury that their jams whip you around before you have time to confirm where you're going. Victory here goes to Brand New for their ability to translate and transform their music expertly to the live stage.
-Emily Kaiser

6:30-7:30 - Battles vs. Lupe vs. Broken Social Scene

Whatever the Lolla powers were thinking when they arranged this set is beyond me. Sure, BSS is a little "safer" and Battles is a littler "nerdier" and Lupe is a little more "a rapper", so you could conceivably separate the massive crowds along such gray lines. But god damn, does nobody win here. Lupe is the hometown favorite, and has the most recent release - but it's still been half a year, and The Cool didn't really bring the hits to further flesh out his (admittedly stellar) live act. Battles also had an explosive year last year, breaking onto the scene with Mirrored and capturing critical acclaim like they'd re-invented music (they only partially did this). Meanwhile, The 'Scene have theoretically been stagnant the longest, letting their various solo outings take precedence since their last full-length. But what if some of those songs make an appearance? What if the band gets Emily Haines to sing "Anthems for A Seventeen Year Old Girl"? What if, OMG, they got FEIST!!! to come out! What if her and Amy got into a fist-fight with Amy Millan? Or better, Amy Winehouse? You can't discount the drama factor here, and that pretty much leaves all these bands as must-sees — for shame, organizers!
-Dan Morgridge

7:30-8:30 - Sharon Jones & The Dap Kings vs. The Toadies

You, me, your brother, your mother, the football team, the nerds, and hopefully one hell of a wedding reception somewhere in the world are all in agreement: they would treat you well, my sweet angel — so help them Jesus. Yes, it's been 14 years since the Toadies tore up the charts with "Possum Kingdom", and damned if there's not a better song to get tens of thousands of people to scream along to in Grant Park.

Unfortunately, as much allure as that single shining moment holds, Todd Lewis's excellent vocals just don't hold a candle to the bar Sharon Jones has set time and time again with her work-a-holic Dap-Kings. The purist retro funk of the Dap-Tone label and the all-star cast of musicians performing simply cannot be missed — especially given that Jones, 52, might concievably slow down in the next few decades (although its not likely). Skip only if the summer heat has severely dehydrated you — Sharon's gonna make you sweat buckets out there.
-Dan Morgridge

Sunday

Sunday 12:15-1:15 - Wild Sweet Orange vs. Kid Sister

Wild Sweet Orange plays roots rock with soul and a sweet honest zing. These Birmingham boys are right in the middle of touring in support of their debut album, We Have Cause to be Uneasy (Canvasback Music July, 29th). Their primary draw is the thoughts and energy of Preston Lovinggood. With outstanding single like “Ten Dead Dogs” and “Wrestle With God” the crowd will be singing and swaying. Even though this is their debut album the band has been together and touring for the last four years. They have refined their live sound and as Preston says “taking all of our experiences and bringing them onstage every night”. I have a rule to never watch folk music at a festival, but Wild Sweet Orange add just enough rock to pass the test.

Kid Sister also has zing, but she is not all that sweet. Her hit song “Pro-nails” has made hardcore hip-hop fans cringe, but her beats and attitude are solid. There have been so few dominant and successful female rappers in hip-hop that I am happy to make it. She has sure aligned herself with the right name, and just as Ice Cube had done for Yo-Yo, Kayne has elevated her game. The question is now will she deliver? I am sure she will put on a fine show, and hip-hop is always great live, but I would recommend Wild Sweet Orange for the simple fact that Kid Sister in from Chicago will be in town more frequently.
-Jason Behrends

3:15-4:30 - Amadou & Miriam vs. Black Kids vs. Chromeo

Let's eliminate Black Kids right away. They're touring again in October with an off day in this region literally three days after Lollapalooza's radius clause expires. (Read: They'll be back around soon.) Despite the excellent "I'm Not Gonna Teach Your Boyfriend How to Dance With You", they're still really raw and kinda shoddy live. The Montreal/New York electrofunk duo Chromeo has experience on big stages and always puts on a fun show with heavy grooves. (Fun fact: Singer David Macklovitch's little brother is Kanye West's DJ.) They're not a bad choice for the electronic-minded. However, Amadou & Mariam bring the goods and this is one of only two US shows for them in 2008. The blind Mali-based duo play African blues tinged with rock riffs, reggae hooks, Latin horns and even some electronic influence (thanks in part to their recent work with Manu Chao). Lollapalooza's always done a pretty good job with international bookings and this year is no exception. Take advantage of it.
-James Ziegenfus

4:15-5:15 - Iron & Wine vs. G. Love & Special Sauce

If you're into Lollapalooza as trip down memory lane festival experience, than surely the mid-'90s hits of Philadelphia-born G. Love & Special Sauce will be the right place for you Sunday afternoon. Known by old and young for their laid back anthems "Baby's Got Sauce" and "Cold Beverage" from their self-titled 1994 release, G. Love has been crafting college radio hits for over a decade. This is certainly one set where you'll want to raise your beer and cry "woo!" alongside the masses.

An equally chill stage this hour will be that occupied by lo-fi rocker Samuel Beam (aka Iron & Wine). You might have first been thrust against Iron & Wine's soothing tunes if you had the soundtrack to the movie Garden State where he covered the otherwise dancy Postal Service song "Such Great Heights", or you might have been lucky enough to catch his collaborative album and tour with southwest indie collective Calexico a few years back. Now working hard under the wing of the Sub Pop label, Iron & Wine isn't so much putting out the lo-fi tapes that brought him notoriety back in the day, but instead is putting out lush, brooding albums like 2007's The Shepherd's Dog. Alternately, if you're into beards, this is the set for you.
-Anne Holub

5-6:15 - Saul Williams vs. Blues Traveler

Pros: Blues Traveler have a frontman (John Popper) who is, to use the vernacular, tanned, rested, and ready. Saul Williams, on the other hand, is a man in a perpetual fighting stance. Blues Traveler just released Cover Yourself in 2007 — it's an album's worth of alternate re-workings of the band's classic songs. That could make their set fun - watch folks all around you screaming for "But Anyway" for five minutes, before realizing that the band is playing "But Anyway." Williams' 2007 album, the brilliantly named The Inevitable Rise and Liberation of Niggy Tardust pretty much tells you whether you need to see this rapper/poet/heir to Gil-Scott Heron and the Last Poets or not. Plus, the album features a baker's dozen of big-name acts, including Trent Reznor, who, ahem ahem, will be playing the fest as well ("unexpected" cameo appearance, anyone?).

Cons: If you go see Blues Traveler, you're going to have to watch a bunch of kids 10 years your younger hopping around to "Runaround" with the same "classic rock" reverence that you reserve for the first four Elvis Costello albums. Similarly, Saul's message-raps may make you feel like you're attending school on the weekend.

Verdict: Unless your mom didn't let you go to H.O.R.D.E. way back when and you're still sore about it, Williams seems a bit fresher.
-Chris Sienko

6:15-7:30 - Love and Rockets vs Girl Talk vs Gnarls Barkley

It's difficult choosing between the post-Bauhaus band, the biomedical engineering mashup DJ and the ex-Goodie Mob vocalist's group with that guy who mixed The Grey Album. Each brings so much to the table. On one stage, you could see a classic '80s alternative rock band. On another, there's... a guy pushing buttons on a laptop while sampling, like, every song that's charted in the US since 1983. And on the other is an inevitable costume party. Love and Rockets may not have the draw that they once did (but neither does Rage and they're even headlining a night), but that won't matter to the fans who've either never seen them or not seen them in 20+ years. Girl Talk will be mixing a hodgepodge of everything, probably a lot from his recent Feed the Animals that's still only available digitally. And even though Gnarls Barkley hit a bit of a sophomore slump with The Odd Couple, they're wonderful entertainers that won't let a few not great songs get in the way of putting on a true performance. You want the classic? Love and Rockets. You want to dance? Girl Talk. You want something to look at? Gnarls Barkley.
- James Ziegenfus

6:15-8 - The National vs. Flosstradamus vs. Mark Ronson

Pros: The National sports two sets of brothers in its five-person lineup, allowing for the possibility of some solid bro-down. Flosstradamus met each other at a party and have been spinning together for almost four years, so you know they're tight like bros. Mark Ronson's last name implies that he's the son of Bowie's A#1 bro from the Ziggy Stardust days, Mick Ronson, but it's not true (though his mom did marry Mick Jones…not of the Clash, but of Foreigner!). The National can break your heart with any number of emotionally wrenching terse strummers from its recent Boxer album. Flosstradamus will break your con-sti-pat-ed no-shuns with its ultra-bumpy club-thumpers, getting your rump muscles warmed up for Kanye (or Trent). Ronson got Ghostface to camero on his first album, and produced Amy Winehouse's Fade To Black, so you know he's got the hookup. Plus, his most recent album, Version, contains re-workings of Brit-Pop hits, the type of which you'd spend $198.73 if you tried to acquire them all individually. Might be a good investment.

Cons: The National's music is created "for those little moments," moments that you might not care to relive when trying for the ecstatic abandon of a three-day rock festival. Flosstradamus could be of limited interest to Chicagoans at the show, as they can see 'em any given weekend around town (if not with a speaker system of this magnitude). Ronson's Britpop revival act may leave you cold if the names Kirsty MacColl or Fun Boy Three don't ring any Pavlov-ian bells.

Verdict: Whether you're finishing off with Trent or Kanye, you're going to be getting a musical talking-to at the end of the festival. I recommend Ronson's generally sunny soul-pop for some pre-catharsis levity.
-Chris Seinko